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XII.  On  the  Action  of  Ammonia  on  Glyoxal. 
By  I)r.  H.  Debus.  Communicated  hy  Professor  Tyndall,  F.B.S. 
Received  May  21, — Read  June  10,  1858. 
If  alcohol  be  slowly  oxidized  at  ordinary  temperatures  by  nitric  acid,  besides  other 
substances,  glyoxal,  CgHgOj,  and  glyoxylic  acid,  C2H4O4*,  are  produced. 
I have  continued  the  investigation  of  these  substances,  and  beg  to  lay  before  the 
Eoyal  Society  some  of  the  more  interesting  results. 
Glyoxal,  of  the  consistency  of  syrup,  is  heated  to  60°  C.,  and  mixed  with  about  three 
times  its  bulk  of  warm  strong  ammonia.  A slight  effervescence  takes  place,  and  the 
liquid  assumes  a brown  colour.  After  a few  minutes  small  crystals  of  an  organic  base, 
which  I shall  call  glycosine,  commence  to  separate.  The  mixture  is  kept  at  a tempera- 
ture of  60°  or  80°  C.,  as  long  as  the  quantity  of  crystals  seems  to  increase.  The  latter 
are  collected  on  a filter  after  the  liquid  has  become  perfectly  cold,  and  washed  with 
cold  water.  The  substances  contained  in  the  brown  mother-liquor  will  be  mentioned 
in  another  part  of  this  paper. 
In  order  to  purify  the  glycosine,  it  is  dissolved  in  diluted  hydrochloric  acid,  the  liquid 
shaken  with  pure  animal  charcoal,  filtered  and  precipitated  by  ammonia.  The  base 
separates  as  a white  ciy^stalline  powder.  This  operation  must  be  repeated  if  the  sub- 
stance should  not  be  quite  colourless.  The  mother-liquor,  from  which  the  pure  glyco- 
sine separates,  contains  only  chloride  of  ammonium. 
Glycosine,  C6H6N4,  obtained  in  the  manner  described,  forms  small  white  prisms, 
which,  when  viewed  with  the  microscope,  appear  iridescent.  It  becomes  electric  on 
being  rubbed  in  a mortar,  and  evaporates  without  melting  when  heated  on  platinum 
foil.  Glycosine,  heated  between  two  watch-glasses  on  a sand-bath,  sublimes  without 
leaving  a residue,  and  produces  magnificent  prisms,  sometimes  of  half  an  inch  in  length. 
The  base  is  inodorous,  tasteless,  and  of  the  softness  of  talc.  In  cold  water  it  is  nearly  . 
insoluble,  and  the  small  quantity  which  is  taken  up  by  hot  water,  separates  almost 
entirely  in  white  needles  when  the  liquid  becomes  cold.  Hydrochloric  and  acetic  acids 
dissolve  glycosine  very  easily ; and  if  the  hydrochloric  acid  solution  be  concentrated  on 
the  water-bath  and  allowed  to  stand,  the  hydrochlorate  presents  itself  in  crystals  some- 
times of  an  inch  in  length,  the  appearance  of  which  resembles  sulphocyanide  of  potas- 
sium. The  hydrochloric  acid  compound  of  glycosine  comports  itself  with  reagents  in 
the  following  manner : — 
I.  Caustic  potash,  ammonia,  and  lime-water  produce  a precipitate  of  glycosine. 
* C=12,  H=l,  0 = 16. — Phil.  Mag.  November  1856,  and  January  1857. 
